JP2990307B2 - Electrophotographic photoreceptor - Google Patents
Electrophotographic photoreceptorInfo
- Publication number
- JP2990307B2 JP2990307B2 JP3110370A JP11037091A JP2990307B2 JP 2990307 B2 JP2990307 B2 JP 2990307B2 JP 3110370 A JP3110370 A JP 3110370A JP 11037091 A JP11037091 A JP 11037091A JP 2990307 B2 JP2990307 B2 JP 2990307B2
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- Japan
- Prior art keywords
- coor
- layer
- photosensitive layer
- compound
- embedded image
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Description
【０００１】[0001]
【産業上の利用分野】本発明は、静電潜像を形成させる
ための電子写真感光体に関する。更に詳述すると、電子
輸送能を有する化合物を含有する層を有する電子写真感
光体に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photosensitive member for forming an electrostatic latent image. More specifically, the present invention relates to an electrophotographic photosensitive member having a layer containing a compound having an electron transporting ability.
【０００２】[0002]
【従来の技術】従来、有機光導電体を用いた電子写真感
光体は、無公害、高生産性、低コスト等の利点があるた
め、種々研究されてきており、実際に、中低速用複写機
の感光体として実用に供されている。これら電子写真感
光体には、積層タイプと単層タイプのものがあるが、有
機光導電体を用いた感光体は一般に光照射により電荷を
発生する電荷発生層と、生じた電荷を輸送する電荷輸送
層からなる積層構造を採っている。この場合、電荷輸送
層に用いられる電荷輸送物質としてはポリ-N-ビニルカ
ルバゾールのような高分子材料や、ピラゾリン、ヒドラ
ゾン、トリフェニルアミン誘導体のような低分子化合物
が用いられている。2. Description of the Related Art Electrophotographic photoreceptors using organic photoconductors have been studied variously because of their advantages such as no pollution, high productivity and low cost. It is practically used as a photoreceptor for machines. These electrophotographic photoreceptors include a laminate type and a single-layer type, and a photoreceptor using an organic photoconductor generally has a charge generation layer that generates charges by light irradiation and a charge generation layer that transports generated charges. It has a laminated structure consisting of a transport layer. In this case, as the charge transporting material used for the charge transporting layer, a polymer material such as poly-N-vinylcarbazole, or a low molecular compound such as a pyrazoline, hydrazone, or triphenylamine derivative is used.
【０００３】しかしながら、これらの電荷輸送物質はい
ずれも正孔輸送能を有するため、感光体の表面を負に帯
電させる現像方式が採られているのがほとんどである。
このため、従来高速機で用いられてきたトナーが利用で
きず、高画質のものが少ないのが現状である。さらにこ
のように感光体表面を負に帯電させる場合、帯電時に空
気中の酸素との反応によりオゾンが発生し環境を害する
ばかりか感光体表面を劣化させるという問題がある。However, since all of these charge transporting substances have a hole transporting property, a development method of negatively charging the surface of a photoreceptor is mostly adopted.
For this reason, the toner conventionally used in high-speed machines cannot be used, and at present, there are few high-quality toners. Further, when the surface of the photoreceptor is negatively charged as described above, ozone is generated due to a reaction with oxygen in the air at the time of charging, and there is a problem that the surface of the photoreceptor is deteriorated as well as harmful to the environment.
【０００４】また、一方では積層感光体の感光層の層構
成を逆にして、電荷輸送層を下側に、電荷発生層を上側
に設けた正帯電用積層感光体が開発されているが、帯電
電位が低く、耐刷性が劣っているため、電荷発生層の上
にさらに保護層を設けるといった構造になっている。[0004] On the other hand, a layered photoconductor for positive charging has been developed in which the layer configuration of the photosensitive layer of the layered photoconductor is reversed, and the charge transport layer is provided on the lower side and the charge generation layer is provided on the upper side. Since the charge potential is low and the printing durability is inferior, a structure is provided in which a protective layer is further provided on the charge generation layer.
【０００５】上記のような問題を解決するためには、電
子輸送能を有する電荷輸送物質を電荷輸送層に用い、さ
らに感光体表面を正に帯電するようにした感光体を構成
すればよい。このような電子輸送性素材としては2,4,7-
トリニトロ-9-フルオレノンが知られている。しかし、
この物質はすべての電子写真感光体に有用なのではな
く、さらに発癌性を有することからその使用が中止され
ている。また、そのほかに有用な素材が少ないのが現状
である。[0005] In order to solve the above-mentioned problems, it is only necessary to construct a photoreceptor in which a charge transporting material having an electron transporting ability is used for the charge transporting layer and the surface of the photoreceptor is positively charged. 2,4,7-
Trinitro-9-fluorenone is known. But,
This substance is not useful for all electrophotographic photoreceptors, and its use has been discontinued due to its carcinogenicity. In addition, there are currently few useful materials.
【０００６】[0006]
【発明の目的】本発明は、上記のような問題点に鑑み、
本発明の目的は、電子輸送能を有する電荷輸送物質を用
いた電子写真感光体を提供することにある。SUMMARY OF THE INVENTION The present invention has been made in view of the above problems,
An object of the present invention is to provide an electrophotographic photoreceptor using a charge transporting substance having an electron transporting ability.
【０００７】本発明の他の目的は、優れた電子写真性能
を有する正帯電用積層型電子写真感光体を提供すること
にある。Another object of the present invention is to provide a positively charged laminated electrophotographic photosensitive member having excellent electrophotographic performance.
【０００８】[0008]
【発明の構成】本発明者らは、研究の結果、本発明の目
的は下記のいづれの電子写真感光体によっても達成され
ることを見出した。即ち、導電性支持体上に感光層を設
けた電子写真感光体において、前記感光層に、電荷輸送
物質として下記一般式（Ａ）〜一般式（Ｄ）で示される
いづれかの化合物を含有することを特徴とする電子写真
感光体。As a result of research, the present inventors have found that the object of the present invention can be achieved by any of the following electrophotographic photosensitive members. That is, in an electrophotographic photosensitive member having a photosensitive layer provided on a conductive support, the photosensitive layer contains any of the compounds represented by the following general formulas (A) to (D) as a charge transporting substance. An electrophotographic photosensitive member characterized by the following.
【０００９】[0009]
【化５】 Embedded image
【００１０】前記一般式（Ａ）において、Ｘは＝C(C
N)2，＝C(H)(CN)，＝C(COOR)2，＝N(CN)，＝C(CN)(COO
R)，＝C(H)(COOR)，＝Oを表す。In the general formula (A), X is = C (C
N) 2 , = C (H) (CN), = C (COOR) 2 , = N (CN), = C (CN) (COO
R), = C (H) (COOR), = O.
【００１１】Ｙ，Ｚは置換又は非置換の次記２つの環
基；芳香族６員環、芳香族複素環を表す。Y and Z each represent the following two substituted or unsubstituted ring groups; an aromatic 6-membered ring and an aromatic heterocyclic ring.
【００１２】[0012]
【００１３】[0013]
【００１４】また前記一般式（Ｃ）において、Ｘは二方
向に結合手の用いた２価の＝N-R，＝O，＝S，＝Seを表
す。Ｙ，Ｚは＝C(CN)2，＝N(CN)，＝Oを表す。またＲ，
Ｒ1はアルキル、アルコキシ、アリール、アシル、エス
テル、アミド、スルホン、スルホンアミドの各基又は水
素原子を表す。またｍはｍ≧０の整数である。In the general formula (C), X represents divalent = NR, = O, = S, = Se using a bond in two directions. Y and Z represent = C (CN) 2 , = N (CN), and = O. Also R,
R 1 represents an alkyl, alkoxy, aryl, acyl, ester, amide, sulfone, sulfonamide group or a hydrogen atom. M is an integer of m ≧ 0.
【００１５】更に前記一般式（Ｄ）において、Ｘ，Ｙは
＝C(CN)2，＝C(H)(CN)，＝C(COOR)2，＝C(H)(COOR)，＝
C(CN)(COOR)，＝N(CN)，＝Oを表す。In the general formula (D), X and Y are CC (CN) 2 , CC (H) (CN), CC (COOR) 2 , CC (H) (COOR),
Represents C (CN) (COOR), = N (CN), = O.
【００１６】Ｒはアルキル、アルコキシ、アリール、ア
シル、エステル、アミドの各基又は水素原子を表す。ま
たｍはｍ≧０の整数である。R represents an alkyl, alkoxy, aryl, acyl, ester, or amide group or a hydrogen atom. M is an integer of m ≧ 0.
【００１７】本発明で用いられる前記一般式（Ａ）〜
（Ｄ）で示される化合物の例としては次のものが例示さ
れる。The above general formulas (A) to (C) used in the present invention.
Examples of the compound represented by (D) include the following.
【００１８】これらの化合物は、通常用いられる合成法
にしたがい合成される。These compounds are synthesized according to commonly used synthesis methods.
【００１９】：一般式（Ａ）で表される化合物： （合成例Ａ）Compound represented by formula (A): (Synthesis Example A)
【００２０】[0020]
【化６】 Embedded image
【００２１】9-オキソ-9H-チオキサンテン-3-カルボニ
トリル10,10-ジオキシド10ｇ（0.037mol）とマロノニト
リル7.85ｇ（0.12mol）を乾燥ピリジン（500ml）中、窒
素雰囲気下、20時間加熱還流した。このときモレキュラ
ーシーブ（３Ａ）20ｇをソックスレー抽出器中に入れ
て、使用した。放冷後減圧下でピリジンを50mlにまで濃
縮し、エーテル（100ml）を加えて、析出した結晶を濾
別し、7.63ｇ（0.024mol，65％）の粗結晶を得た。これ
をアセトンから再結晶し、7.04ｇ（0.022mol，60％）の
目的物を得た。9-oxo-9H-thioxanthene-3-carbonitrile 10 g (0.037 mol) of 10,10-dioxide and 7.85 g (0.12 mol) of malononitrile were heated to reflux in a dry pyridine (500 ml) under a nitrogen atmosphere for 20 hours. did. At this time, 20 g of molecular sieve (3A) was put into a Soxhlet extractor and used. After cooling, pyridine was concentrated to 50 ml under reduced pressure, ether (100 ml) was added, and the precipitated crystals were separated by filtration to obtain 7.63 g (0.024 mol, 65%) of crude crystals. This was recrystallized from acetone to obtain 7.04 g (0.022 mol, 60%) of the desired product.
【００２２】（例示化合物）(Exemplary compounds)
【００２３】[0023]
【化７】 Embedded image
【００２４】[0024]
【化８】 Embedded image
【００２５】[0025]
【化９】 Embedded image
【００２６】[0026]
【化１０】 Embedded image
【００２７】[0027]
【００２８】[0028]
【００２９】[0029]
【００３０】[0030]
【００３１】[0031]
【００３２】[0032]
【００３３】[0033]
【００３４】[0034]
【００３５】：一般式（Ｃ）で表される化合物： （合成例Ｃ）Compound represented by formula (C): (Synthesis Example C)
【００３６】[0036]
【化１６】 Embedded image
【００３７】4,4´-ジブロムチエノチオフェン 10ｇ
（0.033mol）をテトラアシアノエチレンオキシドで処理
し例示化合物Ｃ３3.16ｇ（0.0118mol、36％）を得た。4,4'-dibromothienothiophene 10 g
(0.033 mol) was treated with tetracyanoethylene oxide to obtain 33.16 g (0.0118 mol, 36%) of the exemplified compound C.
【００３８】（例示化合物）(Exemplary compounds)
【００３９】[0039]
【化１７】 Embedded image
【００４０】[0040]
【化１８】 Embedded image
【００４１】[0041]
【化１９】 Embedded image
【００４２】[0042]
【化２０】 Embedded image
【００４３】[0043]
【化２１】 Embedded image
【００４４】：一般式（Ｄ）で表される化合物： （合成例Ｄ）Compound represented by formula (D): (Synthesis Example D)
【００４５】[0045]
【化２２】 Embedded image
【００４６】インデノインデン5,10-ジオン23ｇにノナ
ノイルクロライド 18ｇをＴＨＦ１ｌの中に入れ、ピペ
リジン8.5ｇを加え、室温下24時間撹拌し、後処理の
後、カラムクロマトで精製し、中間化合物を収率18％で
得た。To 23 g of indenoindene 5,10-dione, 18 g of nonanoyl chloride was placed in 1 l of THF, 8.5 g of piperidine was added, and the mixture was stirred at room temperature for 24 hours. Was obtained with a yield of 18%.
【００４７】中間化合物 3.7ｇとマロノニトリル0.07
ｇとをジオキサン100mlの中に入れ、酢酸0.06ｇとピペ
リジン0.09ｇを加え、70℃で８時間撹拌し、後処理の
後、カラムクロマトで精製し、例示化合物（Ｄ２）を収
率19％で得た。3.7 g of the intermediate compound and 0.07 of malononitrile
g in 100 ml of dioxane, 0.06 g of acetic acid and 0.09 g of piperidine were added, and the mixture was stirred at 70 ° C. for 8 hours. After work-up, the product was purified by column chromatography to give Exemplified Compound (D2) in a yield of 19%. Obtained.
【００４８】この化合物は、ＦＤ−ＭＳスペクトルでｍ
／Ｚ＝468を示した。This compound was found to have a m
/ Z = 468.
【００４９】（例示化合物）(Exemplary compounds)
【００５０】[0050]
【化２３】 Embedded image
【００５１】[0051]
【化２４】 Embedded image
【００５２】[0052]
【化２５】 Embedded image
【００５３】[0053]
【化２６】 Embedded image
【００５４】本発明の電子写真感光体において、導電性
支持体としては、たとえば金属パイプ、金属板、金属シ
ート、金属箔、導電処理を施した高分子フィルム、Ａ１
等の金属の蒸着層を設けた高分子フィルム、金属酸化
物、第４級アンモニウム塩等により被覆された高分子フ
ィルムまたは紙等が用いられる。In the electrophotographic photoreceptor of the present invention, the conductive support includes, for example, a metal pipe, a metal plate, a metal sheet, a metal foil, a conductive-treated polymer film, A1
For example, a polymer film provided with a metal deposition layer such as a metal film, a polymer film or paper coated with a metal oxide, a quaternary ammonium salt, or the like is used.
【００５５】本発明の電子写真感光体において、導電性
支持体上には感光層が設けられるが、感光層は単層構造
でもよく、電荷発生層と電荷輸送層とに機能分離された
積層構造のものでもよい。また、導電性支持体と感光層
の間に接着層を設けても良い。In the electrophotographic photoreceptor of the present invention, a photosensitive layer is provided on a conductive support. The photosensitive layer may have a single-layer structure, or a laminated structure in which a charge generation layer and a charge transport layer are functionally separated. It may be. Further, an adhesive layer may be provided between the conductive support and the photosensitive layer.
【００５６】接着層は、樹脂単独で形成したもの、酸化
錫、酸化インジウム、酸化チタンなどの低抵抗化合物を
樹脂中に分散させたものを塗布したもの、または酸化ア
ルミニウム、酸化亜鉛、酸化珪素などの蒸着膜でも良
い。接着層に用いる樹脂としては、特に制限はないが、
塩化ビニリデン−塩化ビニル共重合体、水溶性ポリビニ
ルブチラール樹脂、アルコール可溶性ポリアミド樹脂、
酢酸ビニル系樹脂、ポリビニルアルコール、ニトロセル
ロース、ポリイミド樹脂等が挙げられる。The adhesive layer may be formed of a resin alone, coated with a resin in which a low-resistance compound such as tin oxide, indium oxide, or titanium oxide is dispersed in a resin, or may be formed of aluminum oxide, zinc oxide, silicon oxide, or the like. May be used. The resin used for the adhesive layer is not particularly limited,
Vinylidene chloride-vinyl chloride copolymer, water-soluble polyvinyl butyral resin, alcohol-soluble polyamide resin,
Examples include vinyl acetate resin, polyvinyl alcohol, nitrocellulose, and polyimide resin.
【００５７】結着層の膜厚は0.01〜10μｍ程度が好まし
く、特に0.01〜１μｍが好ましい。感光層が単層の場合
には、たとえばポリビニルカルバゾール等の公知の材料
から構成された感光層中に上記一般式（Ａ）〜（Ｄ）で
示される化合物を増感剤として含有させたもの、または
公知の電荷発生物質を含む感光層中に上記一般式（Ａ）
〜（Ｄ）で示される化合物を電子輸送物質として含有さ
せたものなどが挙げられる。The thickness of the binder layer is preferably about 0.01 to 10 μm, particularly preferably 0.01 to 1 μm. When the photosensitive layer is a single layer, for example, a photosensitive layer composed of a known material such as polyvinyl carbazole and the like, in which the compounds represented by the above general formulas (A) to (D) are contained as a sensitizer; Alternatively, in the photosensitive layer containing a known charge generating substance,
To (D) as an electron transporting substance.
【００５８】一方、感光層が積層型の場合においては、
電荷発生層は電荷発生物質を導電性支持体上に蒸着して
得られたものでもよく、電荷発生物質と結着性樹脂とを
主成分とする塗布液を塗布することによって形成しても
良い。On the other hand, when the photosensitive layer is a laminated type,
The charge generation layer may be obtained by depositing a charge generation substance on a conductive support, or may be formed by applying a coating liquid containing a charge generation substance and a binder resin as main components. .
【００５９】電荷発生物質および結着樹脂としては公知
のものはいづれも使用できる。例えば、電荷発生物質と
してはＴｒｉ−Ｓｅ、などの無機半導体、ポリビニルカ
ルバゾール等の有機半導体、ビスアゾ系化合物、トリス
アゾ系化合物、無金属フタロシアニン系化合物、金属フ
タロシニアン系化合物、ピリリウム系化合物、スクエア
リウム系化合物、シアニン系化合物、ペリレン系化合
物、多環キノン系化合物等の有機顔料が使用できる。ま
た、結着樹脂としては、ポリスチレン、シリコーン樹
脂、ポリカーボネート樹脂、アクリル樹脂、メタクリル
樹脂、ポリエステル、ビニル系重合体、セルロース系樹
脂、ブチラール系樹脂、シリコーン変性ブチラール樹
脂、アルキッド樹脂等が使用できる。Any known charge generating substance and binder resin can be used. For example, as a charge generating substance, an inorganic semiconductor such as Tri-Se, an organic semiconductor such as polyvinyl carbazole, a bisazo compound, a trisazo compound, a metal-free phthalocyanine compound, a metal phthalocyanine compound, a pyrylium compound, and a squarium compound And organic pigments such as cyanine compounds, perylene compounds, and polycyclic quinone compounds. As the binder resin, polystyrene, silicone resin, polycarbonate resin, acrylic resin, methacrylic resin, polyester, vinyl polymer, cellulose resin, butyral resin, silicone-modified butyral resin, alkyd resin and the like can be used.
【００６０】電荷発生層の膜厚は、0.01〜10μｍ程度が
好ましく、特に0.05〜２μｍが好ましい。The thickness of the charge generation layer is preferably about 0.01 to 10 μm, particularly preferably 0.05 to 2 μm.
【００６１】電荷発生層の上には電荷輸送層が形成され
る。この電荷輸送層は、上記一般式（Ａ）〜（Ｄ）で示
される化合物と結着樹脂とで構成されるものであって、
上記一般式（Ａ）〜（Ｄ）で示される化合物、結着樹
脂、および適当な溶剤を主成分とする塗布液を、アプリ
ケータ、バーコータ、ディップコータ等により、電荷発
生層上に塗布することによって形成される。この場合、
各種化合物と結着樹脂との混合比は１：100〜100：１が
好ましく、特に１：20〜20：１が好ましい。A charge transport layer is formed on the charge generation layer. The charge transport layer is composed of the compounds represented by the general formulas (A) to (D) and a binder resin,
Coating a coating solution containing the compounds represented by the above general formulas (A) to (D), a binder resin, and a suitable solvent on the charge generation layer using an applicator, a bar coater, a dip coater, or the like. Formed by in this case,
The mixing ratio between the various compounds and the binder resin is preferably from 1: 100 to 100: 1, and particularly preferably from 1:20 to 20: 1.
【００６２】電荷輸送層に用いる電荷輸送物質および結
着樹脂としては、公知のものはいづれも使用できる。例
えば、結着樹脂としては、アクリロニトリル−ブタジエ
ン共重合体スチレン−ブタジエン共重合体、ビニルトル
エン−スチレン共重合体、スチレン変性アルキッド樹
脂、シリコーン変性アルキッド樹脂、大豆油変性アルキ
ッド樹脂、塩化ビニリデン−塩化ビニル樹脂、ポリビニ
ルブチラール、ニトロ化ポリスチレン、ポリメチルスチ
レン、ポリイソプレン、ポリエステル、フェノール樹
脂、ケトン樹脂、ポリアミド、ポリカーボネート、ポリ
チオカーボネート、ポリアリレート、ポリハロアリレー
ト、酢酸ビニル系樹脂、ポリスチレン、ポリアリルエー
テル、ポリビニルアクリレート、ポリスルホン、ポリメ
タクリレート等が挙げられる。また、電荷輸送層に電子
供与性物質を添加しても良い。さらに、電荷輸送層に酸
化防止剤、ラジカルトラップ剤を添加しても良い。As the charge transporting material and the binder resin used in the charge transporting layer, any known materials can be used. For example, as the binder resin, acrylonitrile-butadiene copolymer styrene-butadiene copolymer, vinyl toluene-styrene copolymer, styrene-modified alkyd resin, silicone-modified alkyd resin, soybean oil-modified alkyd resin, vinylidene chloride-vinyl chloride Resin, polyvinyl butyral, nitrated polystyrene, polymethylstyrene, polyisoprene, polyester, phenolic resin, ketone resin, polyamide, polycarbonate, polythiocarbonate, polyarylate, polyhaloallylate, vinyl acetate resin, polystyrene, polyallyl ether, Examples thereof include polyvinyl acrylate, polysulfone, and polymethacrylate. Further, an electron donating substance may be added to the charge transport layer. Further, an antioxidant and a radical trapping agent may be added to the charge transport layer.
【００６３】電荷輸送層の厚さは、２〜100μｍが好ま
しく、特に５〜50μｍが好ましい。The thickness of the charge transport layer is preferably from 2 to 100 μm, particularly preferably from 5 to 50 μm.
【００６４】なお、本発明の電子写真感光体において
は、導電性支持体の上に障壁層を設けても良い。障壁層
は、導電性支持体からの不要な電荷の注入を阻止するた
めに有効であり、画質を向上させる作用がある。障壁層
を形成する材料としては、酸化アルミニウム等の金属酸
化物あるいは、アクリル樹脂、フェノール樹脂、ポリエ
ステル樹脂、ポリウレタン等がある。障壁層は、接着層
の上に設けてもよく、また、上側に設けても良い。In the electrophotographic photoreceptor of the present invention, a barrier layer may be provided on the conductive support. The barrier layer is effective for preventing injection of unnecessary charges from the conductive support, and has an effect of improving image quality. Examples of a material for forming the barrier layer include a metal oxide such as aluminum oxide, an acrylic resin, a phenol resin, a polyester resin, and a polyurethane. The barrier layer may be provided on the adhesive layer, or may be provided on the upper side.
【００６５】〔実施例〕以下、本発明を実施例Ａ群〜Ｄ
群によって説明する。[Examples] The present invention will now be described with reference to Examples A to D.
Explanation will be given by group.
【００６６】（実施例Ａ群） 実施例Ａ１ アルミニウムを蒸着したＰＥＴフィルム上に、塩化ビニ
ル−酢酸ビニル−無水マレイン酸共重合体よりなる厚さ
0.05μｍの中間層を設け、その上にビスアゾ化合物とポ
リビニルブチラール（ビスアゾ化合物：ブチラール＝
３：１）からなる電荷発生層（0.5μｍ）をバーコータ
を用いて設け、その上に例示化合物Ａ２ 0.16gを塩化エ
チレン10mlに溶解させた溶液（ポリマー：溶媒＝0.75：
１）2ｇをドクターブレードで塗布し、90℃で１時間乾
燥させ、膜厚20μｍの電子写真感光体を作成した。この
電子写真感光体について静電複写紙試験装置（EPA-8100
川口電機製作所（株）製）を用いて＋800Ｖおよび−80
0Ｖに帯電させ、10 luxの白色光を露光し、表面電位が
半分になるまでの露光量を求め、感度とした。(Example A group) Example A1 Thickness of a vinyl chloride-vinyl acetate-maleic anhydride copolymer on a PET film on which aluminum was deposited
A 0.05 μm intermediate layer is provided, and a bisazo compound and polyvinyl butyral (bisazo compound: butyral =
A charge generating layer (0.5 μm) composed of 3: 1) was provided using a bar coater, and a solution of 0.16 g of Exemplified Compound A2 dissolved in 10 ml of ethylene chloride (polymer: solvent = 0.75:
1) 2 g was applied with a doctor blade and dried at 90 ° C. for 1 hour to prepare an electrophotographic photosensitive member having a thickness of 20 μm. For this electrophotographic photoreceptor, an electrostatic copying paper tester (EPA-8100
+800 V and -80 using Kawaguchi Electric Works, Ltd.
It was charged to 0 V, exposed to 10 lux of white light, and the exposure amount until the surface potential was reduced to half was determined as the sensitivity.
【００６７】結果は表Ａに示した。尚感度の求め方は他
の実施例群も同様である。The results are shown in Table A. The method of obtaining the sensitivity is the same for the other examples.
【００６８】実施例Ａ２〜Ａ７ 例示化合物Ａ２の代りにＡに示したような化合物を用い
た以外は、実施例Ａ１と同様にして電子写真感光体を作
成し、同様に感度を測定した。結果を表Ａに示す。Examples A2 to A7 An electrophotographic photosensitive member was prepared in the same manner as in Example A1 except that the compound shown in A was used instead of the exemplified compound A2, and the sensitivity was measured in the same manner. The results are shown in Table A.
【００６９】比較例Ａ（１） 例示化合物Ａ２の代りに2,4,7-トリニトロフルオレノン
（TNF）を用いた以外は実施例Ａ１におけると同様にし
て電子写真感光体を作成し、同様にして感度を測定し
た。結果を表Ａに示す。Comparative Example A (1) An electrophotographic photoreceptor was prepared in the same manner as in Example A1, except that 2,4,7-trinitrofluorenone (TNF) was used instead of Exemplified Compound A2. The sensitivity was measured. The results are shown in Table A.
【００７０】比較例Ａ（２） 例示化合物Ａ２の代りにテトラシアノキノジメタン（TC
NQ）を用いた以外は実施例Ａ１におけると同様にして電
子写真感光体を作成し、同様にして感度を測定した。結
果を表Ａに示す。Comparative Example A (2) In place of Exemplified Compound A2, tetracyanoquinodimethane (TC
An electrophotographic photosensitive member was prepared in the same manner as in Example A1 except that NQ) was used, and the sensitivity was measured in the same manner. The results are shown in Table A.
【００７１】[0071]
【表１】 [Table 1]
【００７２】[0072]
【００７３】[0073]
【００７４】[0074]
【００７５】[0075]
【００７６】[0076]
【００７７】（実施例Ｃ群） 実施例Ｃ１ アルミニウムを蒸着したＰＥＴフィルム上に塩化ビニル
−酢酸ビニル−無水マレイン酸共重合体よりなる厚さ0.
05μｍの中間層を設け、その上にビスアゾ化合物とポリ
ビニルブチラール（ビスアゾ化合物：ブチラール＝３：
１）からなる電荷発生層（0.5μｍ）をバーコータを用
いて設け、その上に例示化合物Ｃ２ 0.16gを塩化エチレ
ン10mlに溶解させた溶液（ポリマー：溶媒＝0.75：１）
２gをドクターブレードで塗布し、90℃で１時間乾燥さ
せ、膜厚20μｍの電子写真感光体を作成した。結果は表
Ｃに示した。(Example C group) Example C1 A film made of a vinyl chloride-vinyl acetate-maleic anhydride copolymer having a thickness of 0.1 mm on a PET film on which aluminum was deposited.
A 05 μm intermediate layer was provided, and a bisazo compound and polyvinyl butyral (bisazo compound: butyral = 3:
A charge generating layer (0.5 μm) composed of 1) was provided using a bar coater, and a solution obtained by dissolving 0.16 g of Exemplified Compound C2 in 10 ml of ethylene chloride (polymer: solvent = 0.75: 1) was formed thereon.
2 g was applied with a doctor blade and dried at 90 ° C. for 1 hour to prepare an electrophotographic photosensitive member having a thickness of 20 μm. The results are shown in Table C.
【００７８】実施例Ｃ２〜Ｃ１２ 例示化合物Ｃ２の代りに表Ｃに示したような化合物を用
いた以外は、実施例Ｃ１と同様にして電子写真感光体を
作成し、同様に感度を測定した。結果を表Ｃに示す。Examples C2 to C12 An electrophotographic photosensitive member was prepared in the same manner as in Example C1 except that the compounds shown in Table C were used instead of the exemplified compound C2, and the sensitivity was measured in the same manner. The results are shown in Table C.
【００７９】比較例Ｃ（１） 例示化合物Ｃ２の代りに2,4,7-トリニトロフルオレノン
（TNF）を用いた以外は実施例Ｃ１におけると同様にし
て電子写真感光体を作成し、同様にして感度を測定し
た。結果を表Ｃに示す。Comparative Example C (1) An electrophotographic photoreceptor was prepared in the same manner as in Example C1 except that 2,4,7-trinitrofluorenone (TNF) was used instead of Exemplified Compound C2. The sensitivity was measured. The results are shown in Table C.
【００８０】比較例Ｃ（２） 例示化合物Ｃ２の代りにテトラシアノキノジメタン（TC
NQ）を用いた以外は実施例Ｃ１におけると同様にして電
子写真感光体を作成し、同様にして感度を測定した。結
果を表Ｃに示す。Comparative Example C (2) In place of Exemplified Compound C2, tetracyanoquinodimethane (TC
An electrophotographic photosensitive member was prepared in the same manner as in Example C1 except that NQ) was used, and the sensitivity was measured in the same manner. The results are shown in Table C.
【００８１】[0081]
【表３】 [Table 3]
【００８２】（実施例Ｄ群） 実施例Ｄ１ アルミニウムを蒸着したＰＥＴフィルム上に塩化ビニル
−酢酸ビニル−無水マレイン酸共重合体よりなる厚さ0.
05μｍの中間層を設け、その上にビスアゾ化合物とポリ
ビニルブチラール（ビスアゾ化合物：ブチラール＝３：
１）からなる電荷発生層（0.5μｍ）をバーコータを用
いて設け、その上に例示化合物Ｄ１ 0.16gを塩化エチレ
ン10mlに溶解させた溶液（ポリマー：溶媒＝0.75：１）
２gをドクターブレードで塗布し、90℃で１時間乾燥さ
せ、膜厚20μｍの電子写真感光体を作成した。結果は表
Ｄに示した。(Example D group) Example D1 A film made of a vinyl chloride-vinyl acetate-maleic anhydride copolymer having a thickness of 0.1 mm on a PET film on which aluminum was deposited.
A 05 μm intermediate layer was provided, and a bisazo compound and polyvinyl butyral (bisazo compound: butyral = 3:
A charge generation layer (0.5 μm) made of 1) was provided using a bar coater, and a solution of 0.16 g of Exemplified Compound D1 dissolved in 10 ml of ethylene chloride (polymer: solvent = 0.75: 1) was formed thereon.
2 g was applied with a doctor blade and dried at 90 ° C. for 1 hour to prepare an electrophotographic photosensitive member having a thickness of 20 μm. The results are shown in Table D.
【００８３】実施例Ｄ２〜Ｄ９ 例示化合物Ｄ１の代りに表Ｄに示したような化合物を用
いた以外は、実施例Ｄ１と同様にして電子写真感光体を
作成し、同様に感度を測定した。結果を表Ｄに示す。Examples D2 to D9 An electrophotographic photoreceptor was prepared in the same manner as in Example D1, except that the compounds shown in Table D were used instead of Exemplified Compound D1, and the sensitivity was measured in the same manner. The results are shown in Table D.
【００８４】比較例Ｄ（１） 例示化合物Ｄ１の代りに2,4,7-トリニトロフルオレノン
（TNF）を用いた以外は実施例Ｄ１におけると同様にし
て電子写真感光体を作成し、同様にして感度を測定し
た。結果を表Ｄに示す。Comparative Example D (1) An electrophotographic photoreceptor was prepared in the same manner as in Example D1 except that 2,4,7-trinitrofluorenone (TNF) was used instead of Exemplified Compound D1. The sensitivity was measured. The results are shown in Table D.
【００８５】比較例Ｄ（２） 例示化合物Ｄ１代りにテトラシアノキノジメタン（TCN
Q）を用いた以外は実施例Ｄ１におけると同様にして電
子写真感光体を作成し、同様にして感度を測定した。結
果を表Ｄに示す。Comparative Example D (2) Exemplified Compound D1 was replaced with tetracyanoquinodimethane (TCN)
An electrophotographic photosensitive member was prepared in the same manner as in Example D1, except that Q) was used, and the sensitivity was measured in the same manner. The results are shown in Table D.
【００８６】[0086]
【表４】 [Table 4]
【００８７】表Ａ〜Ｄに明かなように、本発明の実施例
においては、充分に実用域にある正帯電感度を示してい
る。As is clear from Tables A to D, the examples of the present invention show positive charging sensitivities that are sufficiently in a practical range.
【００８８】[0088]
【発明の効果】本発明の化合物は電子輸送能を有し、実
用性ある正帯電用感光体を提供することができる。The compound of the present invention has an electron transporting ability and can provide a practically usable photosensitive member for positive charging.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) G03G 5/06 314 G03G 5/06 315 ──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int.Cl. 6 , DB name) G03G 5/06 314 G03G 5/06 315
Claims (3)
感光体において、前記感光層に電荷輸送物質として下記
一般式（Ａ）で示される化合物を含有することを特徴と
する電子写真感光体。 【化１】 ［式中、Ｘは＝C(CN)2，＝C(H)(CN)，＝C(COOR)2，＝N
(CN)，＝C(CN)(COOR)，＝C(H)(COOR)，＝Oを表す。Ｙ，
Ｚは置換又は非置換の次記２つの環基；芳香族６員環、
芳香族複素環を表す。］1. An electrophotographic photosensitive member having a photosensitive layer provided on a conductive support, wherein the photosensitive layer contains a compound represented by the following general formula (A) as a charge transporting substance. Photoconductor. Embedded image [Where X is = C (CN) 2 , = C (H) (CN), = C (COOR) 2 , = N
(CN), = C (CN) (COOR), = C (H) (COOR), and = O. Y,
Z is a substituted or unsubstituted following two ring groups; an aromatic 6-membered ring,
Represents an aromatic heterocyclic ring. ]
感光体において、前記感光層に電荷輸送物質として下記
一般式（Ｃ）で示される化合物を含有することを特徴と
する電子写真感光体。 【化３】 ［式中、Ｘは二方向に結合手の開いた２価の＝N-R，＝
O，＝S，＝Seを表す。Ｙ，Ｚは＝C(CN) 2 ，＝N(CN)，＝O
を表す。またＲ 1 はアルキル、アルコキシ、アリ ール、
アシル、エステル、アミド、スルホン、スルホンアミド
の各基又は水素原子を表す。またｍはｍ≧０の整数であ
る。ｍ≧２の場合Ｒ 1 は互に異なっていてもよい。］ 2. An electrophotographic photosensitive member having a photosensitive layer provided on a conductive support, wherein the photosensitive layer contains a compound represented by the following general formula ( C ) as a charge transporting substance. Photoconductor. Embedded image [Wherein X is a bivalent = NR, =
O, = S, = Se. Y and Z are = C (CN) 2 , = N (CN), = O
Represents And R 1 is alkyl, alkoxy, ants Lumpur,
Acyl, ester, amide, sulfone, sulfonamide
Represents a group or a hydrogen atom. M is an integer of m ≧ 0.
You. When m ≧ 2, R 1 may be different from each other. ]
感光体において、前記感光層に電荷輸送物質として下記
一般式（Ｄ）で示される化合物を含有することを特徴と
する電子写真感光体。 【化４】 ［式中、Ｘ，Ｙは＝C(CN) 2 ，＝C(H)(CN)，＝C(COOR) 2 ，
＝C(H)(COOR)，＝C(CN)(COOR)，＝N(CN)，＝Oを表す。
Ｒはアルキル、アルコキシ、アリール、アシル、エステ
ル、アミドの各基又は水素原子を表す。またｍはｍ≧０
の整数である。ｍが≧２の場合Ｒは異なる種類の置換基
でもよい。］ 3. A conductive electrophotographic photoreceptor having a photosensitive layer on a support, an electrophotographic characterized in that it contains the photosensitive layer as a charge-transporting substance represented by the following general formula (D) Compound Photoconductor. Embedded image [Where X and Y are = C (CN) 2 , = C (H) (CN), = C (COOR) 2 ,
= C (H) (COOR), = C (CN) (COOR), = N (CN), = O.
R represents alkyl, alkoxy, aryl, acyl, ester,
And each group of amide or amide or a hydrogen atom. M is m ≧ 0
Is an integer. When m is ≧ 2, R is a different kind of substituent
May be. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3110370A JP2990307B2 (en) | 1991-05-15 | 1991-05-15 | Electrophotographic photoreceptor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3110370A JP2990307B2 (en) | 1991-05-15 | 1991-05-15 | Electrophotographic photoreceptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04338761A JPH04338761A (en) | 1992-11-26 |
| JP2990307B2 true JP2990307B2 (en) | 1999-12-13 |
Family
ID=14534078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3110370A Expired - Lifetime JP2990307B2 (en) | 1991-05-15 | 1991-05-15 | Electrophotographic photoreceptor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2990307B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11495745B2 (en) | 2017-10-20 | 2022-11-08 | Lg Chem, Ltd. | Compound and organic light emitting device comprising same |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07146564A (en) * | 1993-11-24 | 1995-06-06 | Fuji Electric Co Ltd | Electrophotographic photoreceptor |
| DE59508671D1 (en) * | 1994-03-25 | 2000-10-05 | Ciba Sc Holding Ag | Fluorescent dyes containing cyanimino groups |
| TW390883B (en) * | 1994-11-21 | 2000-05-21 | Novo Nordisk As | Azacyclic or azabicyclic compounds for treating diseases in the central nervous system, their preparation and pharmaceutical composition thereof |
| JP3571099B2 (en) * | 1995-03-08 | 2004-09-29 | 京セラミタ株式会社 | Electrophotographic photoreceptor |
| US5840817A (en) * | 1995-12-29 | 1998-11-24 | Samsung Display Devices Co., Ltd. | Polymer for photo-conductive layer and preparation method thereof |
| JPH1090918A (en) * | 1996-07-24 | 1998-04-10 | Konica Corp | Electrophotographic photoreceptor |
| KR100424633B1 (en) * | 1996-12-31 | 2004-05-17 | 삼성에스디아이 주식회사 | Bipolar monolayer-type electrophotographic photoconductor composition |
| US7396622B2 (en) | 2005-06-23 | 2008-07-08 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
| US9048433B2 (en) | 2010-12-17 | 2015-06-02 | Merck Patent Gmbh | Conjugated polymers |
| WO2012146506A1 (en) | 2011-04-28 | 2012-11-01 | Basf Se | Semiconductor materials based on thienothiophene-2,5-dione oligomers and polymers |
| US8431680B2 (en) | 2011-04-28 | 2013-04-30 | Basf Se | Semiconductor materials based on thienothiophene-2,5-dione oligomers and polymers |
| CN103703007A (en) | 2011-07-27 | 2014-04-02 | 默克专利股份有限公司 | Small molecules and their use as organic semiconductors |
| WO2019078620A1 (en) * | 2017-10-20 | 2019-04-25 | 주식회사 엘지화학 | Novel compound and organic light-emitting device using same |
| EP3950665B1 (en) * | 2019-04-01 | 2023-10-04 | Oriental (Luzhou) Agrochemicals. Co., Ltd. | Conjugated triene compound, preparation method therefor and use thereof |
| CN110437103B (en) * | 2019-08-01 | 2021-01-26 | 宁波卢米蓝新材料有限公司 | Cyclic compound, application thereof and electronic device |
| CN113149864B (en) * | 2020-12-29 | 2023-09-12 | 安徽秀朗新材料科技有限公司 | Synthesis and application of thermal activity delay fluorescent material based on indeno [2,1-a ] indene condensed ring unit |
-
1991
- 1991-05-15 JP JP3110370A patent/JP2990307B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11495745B2 (en) | 2017-10-20 | 2022-11-08 | Lg Chem, Ltd. | Compound and organic light emitting device comprising same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04338761A (en) | 1992-11-26 |
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